Best Outdoorsy Travel Destinations for Labor Day Weekend

The summer vacation rush is in full swing. Parents are cashing in on the last chance to get the family together before school starts. Adults are in search of one final beach trip before leaves and snow canvas the ground. Other millennials want to parlay an extra day off from Labor Day into an extended weekend getaway full of Instagram selfies and Snapchat stories.

Then there are the baby boomers (ages 55-74), a segment of the population enjoying retired life. These travelers have no restrictions when seeking places to go on Labor Day weekend. Maybe they want an affordable destination, a quick road trip, or a last-minute getaway as they cross items off the bucket list.

Here, we provide an in-depth guide for Labor Day weekend travel ideas. You’ll find locations geared toward nature and sightseeing enthusiasts. This is for you, you golfers, hikers, and outdoor-loving explorers.

A photo of Pebble Beach Golf Links in Monterey, California.

Monterey, California

You’re likely familiar with this area on the rugged coast of California for one of three reasons: HBO’s hit series “Big Little Lies,” the legendary Pebble Beach Golf Links, or how Clint Eastwood was once mayor of bordering Carmel, California. Whatever the circumstance may be, this is about as California as you can get with rocky shorelines and 50-foot high cliffs.

Play a round of golf at Pebble Peach (or at least check it out because the views are stunning.) Since you’re on the ocean, learn more about what goes on in the Pacific Ocean waters at the Monterey Bay Aquarium. This is a condensed version of the Monterey Bay National Marine Sanctuary, a massive area that covers more than 6,000 square miles from San Francisco to Big Sur. The aquarium features 35,000 creatures as part of 200 exhibits.

Save time for Huckleberry Hill Nature Preserve, full of hiking trails that take you through pine forests with views of the coastline. Whatever you do, don’t forget to hop in a car and wind down 17 Mile Drive, a scenic road that follows the coastline. Rent a car if you don’t have one. Your Facebook friends will thank you later when you post your photos.

Where to stay: The InterContinental Clement Monterey is steps away from the Monterey Bay Aquarium.

A golf course in south Florida.

Palm Beach County, Florida

A popular destination for retirees, Palm Beach County stretches from Jupiter to the north and Boca Raton to the south. You can’t go wrong with any of the beach towns here, whether it’s snorkeling at Phil Foster Park in Riviera Beach or a nighttime stroll on Atlantic Avenue in Delray Beach.

Palm Beach Gardens is home to the PGA of America, so you know golf is serious around these parts. While the focus is on the championship-level courses—PGA National hosts the Honda Classic each year—you can choose from nearly 50 public courses throughout the county. The golf is plentiful here and so are the beaches.

Wakodahactchee Wetlands and the Arthur R. Marshall Loxahatchee National Wildlife Refuge are perfect for an early-morning walk. Keep your eyes peeled for birds, ducks, and alligators. The Lake Trail on Palm Beach island is a way to experience luxury without spending a penny. Soak up the scenes of million-dollar properties and lavish waterfront mansions on this five-mile path.

Where to stay: West Palm Beach and Boca Raton are the more familiar names in the county, but Delray Beach holds its own. This upscale area mixes white sandy beaches with a strip of Atlantic Avenue where happy hours are abundant and drinks are flowing. Stay at The Seagate Hotel and Spa, which is within walking distance of the party.

A beach in Cape Cad, Massachusetts.

Cape Cod, Massachusetts

Naming Cape Cod as a travel destination is like explaining south Florida to someone—it’s broad and expansive. Don’t take that as a negative but rather as a reminder of how many miles wide—65 to be exact—this area covers. You’ll find more than a dozen towns and villages in Cape Cod, each with its own culture and charming quirks. Have a family? Then the Mid Cape, notably Hyannis, Yarmouth, and Dennis, is for you. 

But if you want a less touristy experience and a true Cape Cod feel, head to the Lower Cape, where Harwich and Chatham hug the Nantucket Sound. Make the trek to Bell’s Neck Conservation Lands in Harwich to hike through a mix of marsh and forest. Nickerson State Park in Brewster has eight freshwater ponds for fishing and an eight-mile bike path that connects to the Cape Cod Rail Trail. For golf enthusiasts, play a round at one of Cape Cod’s 27 public courses. Eastward Ho! Country Club in Chatham is ranked by Golf Digest as the No. 7 course in Massachusetts.

Where to stay: The Wequassett Resort and Golf Club in Chatham is one of the more luxurious—and expensive—resorts on the Cape, so we understand if you want a more affordable option such as the DoubleTree by Hilton-Hyannis.

A light house in Montauk, New York.

Montauk, New York

The easternmost part of both New York State and Long Island is known for its fishing culture, state parks, and outdoor recreation in this quaint hamlet. Six parks blend popular fishing destinations with hiking trails. Montauk Point State Park is home to the Montauk Lighthouse, commissioned by President George Washington in 1792. Hit up Hither Hills State Park to explore the walking dunes of Napeague Harbor or Camp Hero State Park for beachfront views and wooded areas that are prime for hiking and biking.

Around Labor Day, you’ll find restaurants and streets buzzing with travelers. Unlike other parts of Long Island such as Southampton, you won’t need a seersucker suit for a dinner reservation. Dine at a seafood spot or go catch your own in the town once known as the “Sport Fishing Capital of the World.”

The August heat warms the Atlantic Ocean waters for all the surfers who flock here. Before you hit the water, set an early tee time at Montauk Downs State Park to take on one of the windiest golf courses in the country.

Where to stay: This boutique spot at Ruschmeyers Hotel is home to 19 cabin-inspired guest rooms.

People walking on the street in Saratoga Springs, New York.

Saratoga Springs, New York

This charming upstate New York getaway captures your attention with a mix of horse racing, music, culture, and outdoor activities. Horse racing drives Saratoga’s economy this time of the year. You’ll find packed bars and restaurants from the thousands of visitors hoping to catch their racing fix since Saratoga Race Course is the oldest major thoroughbred horse race in the country. Labor Day Weekend draws sizable crowds for the Grade 1 Woodward and its $750,000 purse.

Saratoga Spa State Park covers everything from museums and a spa to biking and hiking on 12 miles of trails. Inside the park, grab your clubs and head to Saratoga Spa Golf Course for nine or 18 holes of golf. The park’s crown jewel is arguably Saratoga Performing Arts Center, a hub for dance, theatre, and music. On this particular weekend, you’ll find concerts by Zac Brown Band (Friday, Aug. 30) and Lynyrd Skynyrd (Saturday, Aug. 31).

Where to stay: Stay in the heart of Saratoga at Pavilion Grand Hotel for an upscale, all-suite experience.

A photo of Portland, Oregon, in the fall.

Portland, Oregon

Portland is quickly developing a reputation as one of the top places to retire, so this city is ready-made for travelers seeking a desirable destination. A budding hot spot for foodies and craft beer lovers, Portland embedded its early roots in nature with miles and miles of trails as part of more than 200 parks within its city limits. 

You can say you visited the world’s smallest park at Mill Ends Park—all 24 inches of it. Alternatively, Forest Park is one of the largest urban forests in the country and showcases more than 70 trails. The Oregonian ranks it as the fourth-most iconic hike in Portland, behind Washington Park, Mount Tabor, and Pittock Mansion Hike. Washington Park is home to the Oregon Zoo, where you can visit the Asian elephant and American black bear.

Oregon quietly ranks as one of the top states for golf, as Pacific Dunes and Brandon Dunes came in at No. 2 and No. 7 respectively, in Golf Digest’s list of America’s 100 Greatest Public Courses. (The downfall is those courses are five hours from Portland.) The city can save you a lengthy drive if you play a round at Pumpkin Ridge Golf Club, which boasts both a private (Witch Hollow) and a public (Ghost Creek) course. Both courses have hosted notable tournaments throughout the years, such as the U.S. Amateur, the U.S. Women’s Open, and the Safeway Classic on the LPGA Tour.

Where to stay: The Paramount Hotel is located across the street from Director Park, a popular urban plaza with a distinct canopy.

A view of Lake Tahoe.

Lake Tahoe

While all your friends head to the beach for one last time this summer, travel to the California-Nevada border for a trip to the largest alpine lake in the country. As pristine as this winter-weather haven is for skiing, it also presents stunning views in the summer.

Travelers come here for the typical outdoorsy activities, such as boating, fishing, and hiking. The blue waters—due to low algae concentration levels—and beaches aren’t bad, either, and the trails are extensive. They range from beginner loops a mile or two in length to the Mount Tallac Trail, a “difficult” level 10.2-mile trek that leads to some of the best lake views. (But the work is worth it for that vista!) Head to Emerald Bay State Park at sunrise or sunset to see the sun shimmer on the blue hues of Lake Tahoe.

Where to stay: Enjoy a vacation club setting with the rustic feel of your own personal mountainous cabin at Marriott’s Timber Lodge.

The harbor at Hilton Head Island, South Carolina.

Hilton Head, South Carolina

Hilton Head is so much more than one of the top beach destinations. This island town is a major golf destination thanks to more than 24 championship courses. Harbour Town Golf Links, home to the PGA Tour’s RBC Heritage event each April, is the star attraction. In addition, the close proximity to water naturally makes it a fishing, boating, and sailing hot spot. More than 50 miles of paved paths make biking an easy way to explore the area. Nature lovers can test out more than 14 hiking and biking trails at Pinckney Island National Wildlife Refuge.

You don’t have to be a scratch golfer to visit here, though. Be sure to experience Lowcountry cuisine, whether that’s a belly full of shrimp and grits, she-crab soup, or Frogmore stew.

Where to stay: You’ll have to pay a pretty penny to stay in the southern part of Hilton Head near Harbor Town. Save a few bucks for the grandchildren by staying at the Grand Hilton Head Inn.

Do any of these Labor Day Weekend destinations inspire you? If so, let us help you plan your next trip. We compare loyalty rates from our hotel partners around the globe. If you see something you like, we’ll take you right to the hotel’s website to complete the booking process. We’ll filter out the nonsense so you can get on with your travel. No tricks, just great search.